Lithium hydroxide, monohydrate → HCID 22858020, compound

HRID 2260386Notes

Reaction equation

HRID 2260386 reaction equation
O.[OH-].[Li+].[C:4]([O:8][C:9]([N:11]1[C@@H:15]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[C@H:14]([C:23]([O:25]CC)=[O:24])[O:13][C:12]1([CH3:29])[CH3:28])=[O:10])([CH3:7])([CH3:6])[CH3:5]>O.C(O)C>[C:4]([O:8][C:9]([N:11]1[C@@H:15]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[C@H:14]([C:23]([OH:25])=[O:24])[O:13][C:12]1([CH3:29])[CH3:28])=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 54268998HCID 54268998, compound

Product 1

HCID 22858020HCID 22858020, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 0.19 g of lithium hydroxide hydrate in 3 cm3 of distilled water is added at a temperature in the region of 25° C. to a solution of 0.54 g of ethyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(4-methylphenyl)-5-oxazolidinecarboxylate in 10 cm3 of ethanol. The reaction medium is stirred for 20 minutes at a temperature in the region of 25° C. and then concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. The residue obtained is dissolved in 3.5 cm3 of distilled water and then extracted with 2 times 1 cm3 of diisopropyl ether. The aqueous phase is then acidified to a pH in the region of 1 with 5 cm3 of 1N aqueous hydrochloric acid solution and thereafter extracted with 3 times 4 cm3 of dichloromethane. The organic phases are combined, dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. 0.43 g of (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(4-methylphenyl)-5-oxazolidinecarboxylic acid is thereby obtained in the form of an orange-colored oil.

Workup

  1. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C
  2. customThe residue obtained
  3. extractionextracted with 2 times 1 cm3 of diisopropyl ether
  4. extractionextracted with 3 times 4 cm3 of dichloromethane
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-dd325d28af2c446dbecc279368c496d6
Source dataset
uspto-grants-1995_12
Patent number
US05476954

Reaction notes

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